Outfits to Wear With Stilettos

Pair stilettos with cigarette pants for a crisp, modern style.
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Stiletto heels reach to the sky while adding inches to your height, but a variety of outfit options can bring this sexy staple back down to Earth. These heels can work for daytime casual as well as date night. Tone down the sexiness of other pieces in your outfit to expand the possibilities of the stiletto.

1 Skirt Spectrum

These sexy shoes are a natural complement for mini dresses and evening wear. Make cocktail hour a little sexier by switching your office heels out for stilettos, wearing them with a slim pencil skirt or suit. Create a flirty summertime look by matching stilettos with a short, swingy floral sundress and a straw clutch.

2 Dress Up Denim

To take your skinny jeans from daytime to evening, pair them with stilettos to lengthen out your legs even more. Add a silky tank top, a drapey blouse or a cool cashmere cardigan to keep the look fashion-forward. If you're wearing boot-cut or flare-leg jeans, keep your top slim-fitting and consider a stiletto with a chunky platform to peek out from underneath.

3 Casual Heels

Stilettos bring a funky edge to an outfit that might usually be paired with sneakers. Sky-high heels can be matched up with jean shorts and a button-down shirt. Try a velour tracksuit with slim pants and a relaxed hoodie, adding big shades and a sumptuous leather bag to amp up the glam factor.